Hey Everybody-

Thanks for all of your comments and feedback. It's very helpful.

On the clearance issue, check these photos out.

Front Wheel Clearance:



Rear Wheel Clearance at Chainstay (this is the biggest issue):



As for the rest of the bike...this is what I have done/planned:

1. DONE: Put 8 speed cassette on old Mavic CXP-23s (Leftovers from another upgraded bike)
2. DONE: Installed vintage Sugino (170) 34x45 compact crankset (Purchased a few months back)
3. PLANNED: Remove Simplex 6 speed derailluer, tap hanger, install 8/9 speed centaur (need to purchase)
4. PLANNED: Install 8 speed Daytona brifters (Leftovers from another upgraded bike)

Done! If it doesn't work out, I can put slicks on it and it's my rain bike...actually...either way it's my rain bike.

Believe it or not, the only issue with the Simplex derailluer is that it brushes against the spokes when in the largest cog...which is a little scary...so I've been avoiding it.